US2021206727A1PendingUtilityA1
Deterrents for arthropods and marine organisms
Assignee: UNIV OF NORTH TEXAS HEALTH SCIENCE CENTER AT FORT WORTHPriority: Oct 30, 2017Filed: Sep 3, 2020Published: Jul 8, 2021
Est. expiryOct 30, 2037(~11.2 yrs left)· nominal 20-yr term from priority
Inventors:John A. Schetz
A01N 43/50C07D 233/64A01N 33/10A61K 31/506A61K 45/06A61P 35/00A61K 31/137C07C 225/10A61K 31/4164A61K 31/135A61K 31/4174
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Claims
Abstract
The present invention relates to compounds, compositions, methods of use, and processes for preparing compounds, which are useful as deterrents for terrestrial arthropods and marine organisms.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . A compound of Formula (I) or a salt thereof:
wherein A 1 , A 2 , and A 3 are independently selected from a group consisting of carbon, nitrogen, oxygen, and sulfur;
R 1 and R 2 are independently selected from a group consisting of hydrogen, deuterium, hydroxyl, C 1 -C 6 substituted or unsubstituted alkyl, C 2 -C 6 substituted or unsubstituted alkenyl, C 1 -C 6 substituted or unsubstituted alkoxy; or R 1 and R 2 may be taken together to form a C 1 -C 6 substituted or unsubstituted alkenyl, or ═O; and
R 3 , R 4 , R 5 , R 6 , and R 7 are independently selected from a group consisting of hydrogen, deuterium, halogen, hydroxyl, C 1 -C 6 substituted or unsubstituted alkoxy, C 1 -C 6 substituted or unsubstituted alkyl, R 1 and R 3 may be taken together to form a C 1 -C 6 substituted or unsubstituted cycloalkyl, or C 2 -C 6 substituted or unsubstituted cycloalkenyl, R 2 and R 3 may be taken together to form a C 1 -C 6 substituted or unsubstituted cycloalkyl, or C 2 -C 6 substituted or unsubstituted cycloalkenyl, or R 3 and R 4 may be taken together to form a C 1 -C 6 substituted or unsubstituted cycloalkyl, C 2 -C 6 substituted or unsubstituted cycloalkenyl, or substituted or unsubstituted aryl.
2 . The compound of claim 1 , wherein A 1 is nitrogen, and A 2 and A 3 are carbon.
3 . The compound of claim 1 , wherein A 3 is nitrogen, and A 1 and A 2 are carbon.
4 . The compound of claim 1 , wherein A 1 and A 2 are nitrogen, and A 3 is carbon.
5 . The compound of claim 1 , wherein A 1 and A 3 are nitrogen, and A 2 is carbon.
6 . The compound of claim 1 , wherein A 1 , A 2 , and A 3 are nitrogen.
7 . The compound of claim 1 , wherein R 1 and R 2 are independently selected from a group consisting of hydrogen, deuterium, hydroxyl, C 1 -C 4 substituted or unsubstituted alkyl, C 1 -C 4 substituted or unsubstituted alkenyl, C 1 -C 4 substituted or unsubstituted alkoxy; or R 1 and R 2 may be taken together to form a C 1 -C 4 substituted or unsubstituted alkenyl, or ═O.
8 . The compound of claim 2 , wherein R 1 and R 2 are independently selected from a group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, methoxy, ethoxy, propoxy, isopropoxy, hydroxyl, —CH 2 CH═CH 2 , —CH 2 C(CH 3 )═CH 2 , —CH═C(CH 3 ) 2 , —CH═CHCH 3 ; or R 1 and R 2 may be taken together to form ═CH 2 , ═CHCH 3 , ═C(CH 3 ) 2 , or ═O.
9 . The compound of claim 3 , wherein R 1 and R 2 are independently selected from a group consisting hydrogen, methyl, methoxy, hydroxyl, —CH 2 CH═CH 2 , —CH═CHCH 3 ; or R 1 and R 2 may be taken together to form ═CH 2 , ═CH—CH 3 , or ═O.
10 . The compound of claim 1 , wherein R 3 and R 4 are independently selected from a group consisting of hydrogen, deuterium, halogen, C 1 -C 4 substituted or unsubstituted alkyl, C 1 -C 4 substituted or unsubstituted alkoxy, or R 3 and R 4 may be taken together to form a C 1 -C 5 substituted or unsubstituted cycloalkyl, C 3 -C 5 substituted or unsubstituted cycloalkenyl, substituted or unsubstituted aryl.
11 . The compound of claim 10 , wherein R 3 and R 4 are independently selected from a group comprising hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl, bromine, chlorine, or fluorine, or R 3 and R 4 may be taken together to form a cyclopropyl, cyclobutyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, or aryl.
12 . The compound of claim 11 , wherein R 3 and R 4 are independently selected from a group comprising hydrogen, deuterium, methyl, trifluoromethyl, chlorine, fluorine, or R3 and R 4 may be taken together to form aryl.
13 . The compound of claim 1 , wherein R 1 and R 3 may be taken together to form a C 2 -C 4 substituted or unsubstituted cycloalkyl, or C 2 -C 4 substituted or unsubstituted cycloalkenyl, or R 2 and R 3 may be taken together to form a C 2 -C 4 substituted or unsubstituted cycloalkyl, or C 2 -C 4 substituted or unsubstituted cycloalkenyl.
14 . The compound of claim 13 , wherein R 1 and R 3 may be taken together to form a cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, or cyclohexenyl, or R 2 and R 3 may be taken together to form a cyclopropyl, cyclobutyl, cyclohexyl, cycloheptyl, cyclopentenyl, or cyclohexenyl.
15 . The compound of claim 14 , wherein R 1 and R 3 may be taken together to form a cyclopentyl or cyclohexyl, or R 2 and R 3 may be taken together to form a cyclopentyl or cyclohexyl.
16 . The compound of claim 1 , wherein R 5 , R 6 , and R 7 are independently selected from a group consisting of hydrogen, deuterium, halogen, C 1 -C 4 substituted or unsubstituted alkyl, or C 1 -C 4 substituted or unsubstituted alkoxy.
17 . The compound of claim 16 , wherein R 5 , R 6 , and R 7 are independently selected from a group consisting of hydrogen, deuterium, methyl, ethyl, chlorine, or fluorine.
18 . The compound of claim 17 , wherein R 5 , R 6 , and R 7 are hydrogen or deuterium.
19 . The compound of claim 1 , wherein the compound is selected from a group comprising:
20 . The compound of claim 1 , wherein the compound has a calculated boiling point of greater than 270° C. wherein the calculated boiling point was determined by EPI Suite version 4.11.
21 . The compound of claim 1 , wherein the compound has an EC 50 potency of less than 1 μM.
22 . The compound of claim 21 , wherein the compound has an EC 50 potency of less than 100 nM.
23 . The compound of claim 22 , wherein the compound has an EC 50 potency of less than 10 nM.
24 . The compound of claim 1 , wherein the compound is at least 35 times more selective for an arthropod octopamine receptor than for a human alpha-2 adrenergic receptor.
25 . The compound of claim 24 , wherein the compound is at least 100 times more selective for an arthropod octopamine receptor than for a human alpha-2 adrenergic receptor.
26 . The compound of claim 25 , wherein the compound is at least 500 times more selective for an arthropod octopamine receptor than for a human alpha-2 adrenergic receptor.
27 . The compound of claim 26 , wherein the compound is at least 1,000 times more selective for an arthropod octopamine receptor than for a human alpha-2 adrenergic receptor.
28 . A process for preparing a compound of Formula (I), the process comprising:
a. contacting a compound of Formula (III) with a compound of Formula (IV) to form a compound of Formula (V); and b. contacting a compound of Formula (V) with a compound of Formula (VI) in the presence of a base to corm a compound of Formula (I) according to the following reaction scheme:
wherein:
A 1 , A 2 , A 3 , and A 4 are independently selected from a group consisting of C, N, O, and S;
R 1 and R 2 are taken together as ═O;
R 3 , R 4 , R 5 , R 6 , and R 7 are independently selected from a group consisting of hydrogen, deuterium, halogen, hydroxyl, C 1 -C 6 substituted or unsubstituted alkoxy, C 1 -C 6 substituted or unsubstituted alkyl, or R 3 and R 4 may be taken together to form a C 1 -C 5 substituted or unsubstituted cycloalkyl, C 2 -C 6 substituted or unsubstituted cycloalkenyl, substituted or unsubstituted aryl; and R 8 and R 9 are independently selected from a group consisting of hydrogen, C 1 -C 6 substituted or unsubstituted alkyl; and X is a halogen.
29 . The process of claim 28 , wherein A 1 and A 2 are N, A 3 is C, and A 4 is hydroxy or A 1 and A 3 are N, A 2 is C, and A 4 is hydroxyl; R 1 and R 2 may be taken together as ═O; R 3 and R 4 are independently selected from a group consisting of hydrogen, deuterium, halogen, C 1 -C 4 substituted or unsubstituted alkyl, C 1 -C 4 substituted or unsubstituted alkoxy, or R 3 and R 4 may be taken together to form a C 1 -C 5 substituted or unsubstituted cycloalkyl, or C 3 -C 5 substituted or unsubstituted cycloalkenyl; R 5 , R 6 , and R 7 are independently selected from a group consisting of hydrogen, deuterium, halogen, C 1 -C 4 substituted or unsubstituted alkyl, or C 1 -C 4 substituted or unsubstituted alkoxy; R 8 and R 9 are independently selected from a group consisting of C 1 -C 4 substituted or unsubstituted alkyl; and X is a chlorine, bromine, or iodine.
30 . The process of claim 28 , wherein A 1 and A 2 are nitrogen, A 3 is carbon, and A 4 is hydroxyl or A 1 and A 3 are nitrogen, A 2 is carbon, and A 4 is hydroxyl; R 1 and R 2 may be taken together as ═O; R 3 and R 4 are independently selected from a group consisting of hydrogen, deuterium, methyl, trifluoromethyl, chlorine, fluorine; R 5 , R 6 , and R 7 are independently selected from a group consisting of hydrogen, deuterium, methyl, ethyl, chlorine, or fluorine; R 8 and R 9 are independently selected from a group consisting of methyl, ethyl, or propyl; and X is iodine.
31 . The process of claim 28 , wherein the compound of Formula (IV) is N,O-dimethylhydroxylamine or an acceptable salt thereof.
32 . The process of claim 28 , wherein the compound of Formula (VI) is selected from a group consisting of 4-Iodo-1-tritylimidazole.
33 . The process of claim 28 , wherein the compound of Formula (III) and the compound of Formula (IV) are present at a molar ratio of 1.0:0.5 to about 1.0:2.0 in Step A.
34 . The process of claim 33 , wherein Step A further comprises contact with an acyl coupling reagent; and the compound of Formula (III) and the acyl coupling reagent are present at a molar ratio of 1.0:0.75 to 1.0:2.0.
35 . The process of claim 33 , wherein the process of Step A is conducted at a temperature from about 0° C. to 150° C.
36 . The process of claim 33 , wherein the acyl coupling reagent is chosen from a group consisting of thionyl chloride, oxalyl chloride, phosphorus pentachloride, phosphorus oxychloride, phosphorus trichloride, cyanuric chloride, diphenylphosphonic azide, carbonyl diimidazole, carbonyl ditriazole, carbodiimide, an anhydride, a mixed anhydride, a boron reagent, phosphonium salts, or combinations thereof.
37 . The process of claim 36 , wherein the acyl coupling reagent is a carbodiimide.
38 . The process of claim 28 , wherein Step A is conducted in the presence of a solvent chosen from a polar aprotic solvent, a non-polar aprotic solvent, or combinations thereof.
39 . The process of claim 28 , wherein the compound of Formula (V) and the compound of Formula (VI) are present at a molar ratio of 1.0:0.5 to about 1.0:2.0 in Step B.
40 . The process of claim 28 , wherein Step B further comprises contact with a Grignard Reagent, and the compound of Formula (VI) and the Grignard reagent are present in a molar ratio of 1.0:0.75 to 1.0:2.0.
41 . The process of claim 28 , wherein Step B is conducted in the presence of a solvent chosen from a polar aprotic solvent, a non-polar aprotic solvent, or combinations thereof.
42 . The process of claim 28 , wherein the process of Step B is conducted at a temperature of −78° C. to 100° C.
43 . The process of claim 28 , wherein the compound of Formula (Ia) is converted into the compound of Formula (Ib) according to the following reaction scheme:
wherein R 10 and R 11 of Formula (Ib) independently selected from a group consisting of hydrogen, deuterium, hydroxyl, C 1 -C 6 substituted or unsubstituted alkyl, C 2 -C 6 substituted or unsubstituted alkenyl, C 1 -C 6 substituted or unsubstituted alkoxy; R 10 and R 11 may be taken together to form a C 2 -C 6 substituted or unsubstituted alkenyl; R 3 and R 10 may be taken together to form a C 1 -C 6 substituted or unsubstituted cycloalkyl, or C 2 -C 6 substituted or unsubstituted cycloalkenyl, R 3 and R 11 may be taken together to form a C 1 -C 6 substituted or unsubstituted cycloalkyl, or C 2 -C 6 substituted or unsubstituted cycloalkenyl.
44 . The process of any of the claim 43 , wherein R 10 and R 11 of Formula (Ib) are converted into a group independently selected from a group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, methoxy, ethoxy, propoxy, isopropoxy, hydroxyl, —CH 2 CH═CH 2 , —CH 2 C(CH 3 )═CH 2 , —CH═C(CH 3 ) 2 , —CH═CHCH 3 ; or R 10 and R 11 may be taken together to form ═CH 2 , ═CHCH 3 , or ═C(CH 3 ) 2 ; R 3 and R 10 may be taken together to form a cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, R 3 and R 11 may be taken together to form a cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl.
45 . The process of claim 43 , wherein the reagent for converting R 1 and R 2 of Formula (Ia) into R 10 and R 11 of Formula (Ib) comprises contacting the compound of Formula (Ia) with a reducing agent, a Wittig reagent, an alkyl halide, or combinations thereof.
46 . The process of claim 28 , wherein the compound of Formula (Ia) or Formula (Ib) is converted into a pharmaceutically acceptable salt.
47 . A compound of Formula (II) or a salt thereof:
wherein A 1 is selected from a group consisting of nitrogen, oxygen, and sulfur;
R 1 , R 2 , and R 3 are independently selected from a group is selected from a group consisting of hydrogen, hydroxyl, C 1 -C 6 substituted or unsubstituted alkyl; C 1 -C 6 substituted or unsubstituted alkenyl, C 1 -C 6 substituted or unsubstituted alkoxy, and R 4 , R 5 , R 6 , R 7 , and R 8 are independently selected from a group comprising of hydrogen, halogen, C 1 -C 6 alkyl, C 1 -C 6 halogenated alkyl, or R 1 and R 2 may be taken together to form a C 2 -C 4 substituted or unsubstituted alkenyl, or ═O.
48 . The compound of claim 47 , wherein A 1 is oxygen.
49 . The compound of claim 47 , wherein R 1 , R 2 , and R 3 are independently selected from a group is selected from a group consisting of hydrogen, hydroxyl, C 1 -C 4 substituted or unsubstituted alkyl, C 1 -C 4 substituted or unsubstituted alkenyl, C 1 -C 4 substituted or unsubstituted alkoxy, or R 1 and R 2 may be taken together to form a C 2 -C 4 substituted or unsubstituted alkenyl, or ═O.
50 . The compound of claim 49 , wherein R 1 , R 2 , and R 3 are independently selected from a group is selected from a group consisting of —H, —CH 3 , —OH, —CH 2 NH 2 , —CHCH 3 NH 2 , —C(CH 3 ) 2 NH 2 , —CH 2 NHCH 3 , —CH 2 N(CH 3 ) 2 , —CH 2 OH, —CHCH 3 OH, C(CH 3 ) 2 OH, —CH 2 OCH 3 , —CH 2 OCH 2 CH 3 , —CH 2 CN, —CH(CN) 2 , —CH 2 CH 2 F, —CH 2 CHF 2 , —CH 2 CF 3 , —CH 2 CH 2 C 1 , —CH 2 CHCl 2 , —CH 2 CCl 3 , —CH 2 SOCH 3 , —CH 2 SO 2 CH 3 , —CH(OH)CH 2 NH 2 , —CCH 3 OHCH 2 NH 2 , —CH(OH)CH 2 N(CH 3 ) 2 , —CH(OH)CH 2 NHCH 3 , —CH(OH)CH 2 NHCH(CH 3 ) 2 , —CH(OH)CH 2 NHCH 2 CH 2 CH 3 , —CH(OH)CH 2 NHCH(CH 3 )CH 2 CH 3 , —CH(OH)CH 2 NHCH(CH 3 )CH 2 CH 2 C 6 H 5 , —CH(OH)CH 2 NHCH(CH 3 )CH 2 CH 2 C 6 H 4 OH.
51 . The compound of claim 47 , wherein R 4 is selected from a group consisting hydrogen or C 1 -C 4 substituted or unsubstituted alkyl.
52 . The compound of claim 51 , wherein R 4 is selected from a group consisting of hydrogen, methyl, ethyl, propyl, or isopropyl.
53 . The compound of claim 53 , wherein R 4 is hydrogen.
54 . The compound of claim 47 , wherein R 5 , R 6 , R 7 , and R 8 are independently selected from a group consisting of hydrogen, halogen, C 1 -C 4 substituted or unsubstituted alkyl, or C 1 -C 4 halogenated alkyl.
55 . The compound of claim 54 , wherein R 5 , R 6 , R 7 , and R 8 each independently selected from a group consisting of hydrogen, iodine, bromine, chlorine, fluorine, methyl, fluoromethyl, difluoromethyl, or trifluoromethyl.
56 . The compound of claim 47 , wherein the compound is selected from a group comprising:
57 . The compound of claim 47 , wherein the compound has a calculated boiling point of greater than 270° C.
58 . The compound of claim 47 , wherein the compound has an EC 50 potency of less than 1 μM.
59 . The compound of claim 58 , wherein the compound has an EC 50 potency of less than 100 nM.
60 . The compound of claim 58 , wherein the compound has an EC 50 potency of less than 10 nM.
61 . An arthropod deterrent composition comprising:
a) at least one of an effective amount of the arthropod deterrent of the compound of Formula (II) or a salt thereof;
b) at least one additional component selected from a group comprising fragrances, solvents, diluents, fixatives, carrier, paints, coatings, or combinations thereof;
wherein A 1 is selected from a group consisting of nitrogen, oxygen, and sulfur;
R 1 , R 2 , and R 3 are independently selected from a group is selected from a group consisting of hydrogen, hydroxyl, C 1 -C 6 substituted or unsubstituted alkyl; C 1 -C 6 substituted or unsubstituted alkenyl, C 1 -C 6 substituted or unsubstituted alkoxy; and
R 4 , R 5 , R 6 , R 7 , and R 8 each independently selected from a group comprising of hydrogen, halogen, C 1 -C 6 alkyl, C 1 -C 6 halogenated alkyl, or R 1 and R 2 may be taken together to form a C 2 -C 4 substituted or unsubstituted alkenyl, or ═O.
62 . The composition of claim 61 , wherein A 1 is oxygen.
63 . The composition of claim 61 , wherein R 1 , R 2 , and R 3 are independently selected from a group is selected from a group consisting of hydrogen, hydroxyl, C 1 -C 4 substituted or unsubstituted alkyl, C 1 -C 4 substituted or unsubstituted alkenyl, or C 1 -C 4 substituted or unsubstituted alkoxy.
64 . The composition of claim 63 , wherein R 1 , R 2 , and R 3 are independently selected from a group is selected from a group consisting of —H, —CH 3 , —OH, —CH 2 NH 2 , —CHCH 3 NH 2 , —C(CH 3 ) 2 NH 2 , —CH 2 NHCH 3 , —CH 2 N(CH 3 ) 2 , —CH 2 OH, —CHCH 3 OH, C(CH 3 ) 2 OH, —CH 2 OCH 3 , —CH 2 OCH 2 CH 3 , —CH 2 CN, —CH(CN) 2 , —CH 2 CH 2 F, —CH 2 CHF 2 , —CH 2 CF 3 , —CH 2 CH 2 C 1 , —CH 2 CHCl 2 , —CH 2 CCl 3 , —CH 2 SOCH 3 , —CH 2 SO 2 CH 3 , —CH(OH)CH 2 NH 2 , —CCH 3 OHCH 2 NH 2 , —CH(OH)CH 2 N(CH 3 ) 2 , —CH(OH)CH 2 NHCH 3 , —CH(OH)CH 2 NHCH(CH 3 ) 2 , —CH(OH)CH 2 NHCH 2 CH 2 CH 3 , —CH(OH)CH 2 NHCH(CH 3 )CH 2 CH 3 , —CH(OH)CH 2 NHCH(CH 3 )CH 2 CH 2 C 6 H 5 , —CH(OH)CH 2 NHCH(CH 3 )CH 2 CH 2 C 6 H 4 OH.
65 . The composition of claim 61 , wherein R 4 is selected from a group consisting hydrogen or C 1 -C 4 substituted or unsubstituted alkyl.
66 . The composition of claim 65 , wherein R 4 is selected from a group consisting of hydrogen, methyl, ethyl, propyl, or isopropyl.
67 . The composition of claim 66 , wherein R 4 is hydrogen.
68 . The composition of claim 61 , wherein R 5 , R 6 , R 7 , and R 8 are each independently selected from a group consisting of hydrogen, halogen, C 1 -C 4 substituted or unsubstituted alkyl, or C 1 -C 4 halogenated alkyl.
69 . The composition of claim 61 , wherein R 5 , R 6 , R 7 , and R 8 each independently selected from a group consisting of hydrogen, iodine, bromine, chlorine, fluorine, methyl, fluoromethyl, difluoromethyl, or trifluoromethyl.
70 . The composition of claim 61 , wherein the compound is selected from a group comprising:
71 . The composition of claim 61 , arthropod deterrent of the compound of Formula (II) or a salt thereof ranges from about 0.0001% to 100% (w/w) of the total composition.
72 . The composition of claim 61 , wherein the composition further comprises at least one compound selected from a group comprising N,N-diethyl-meta-toluamide, 1-(1-methylpropoxycarbonyl)-2-(2-hydroxyethyl)piperidine, para-menthane-3,8-diol (PMD, active in Oil of Eucalyptus), ethyl 3-[acetyl(butyl)amino]propanoate, (2S)-1-[(1S)-cyclohex-3-en-1-ylcarbonyl]-2-methylpiperidine, essential oils, etc. for terrestrial arthropods, and copper, zinc and other metals and their oxides, 3-(3,4-dichlorophenyl)-1,1-dimethylurea, 2-methylthio-4-tert-butylamino-6-cyclopropylamino-s-triazine), zincpyrothione (Zinc, Ms(I-hydroxy-2(IH)-pyridinethionato-O,S)—, (T-4)-), copper pyrothione (Copper, Ms(I-hydroxy-2(IH)-pyridinethionato-O,S)—, (T-4)-), diclofluanide (N′-dimethyl-N-phenylsulphamide), zinc ethylene bisdithiocarbamate, zinc bis(dimethylthiocarbamates)) (3-5), quaternary ammonium compounds, 4,5-dichloro-2-n-octyl-3(2H)-isothiazolone, 2-(p-chlorophenyl)-3-cyano-4-bromo-5-trifluoromethyl, or combinations thereof.
73 . The composition of claim 61 , wherein the composition is delivered as a spray, an aerosol, a gel, a cream, a lotion, a coating, or a paint.
74 . A method of deterring marine biofouling organism, the method comprises
a) providing a composition of claim 61 ; and b) treating a surface or an aqueous solution with the composition; and c) curing the composition; marine organism is selected from a group consisting of barnacles, tubeworms, bivalves, marine maxillopoda, Polychaeta, bivalvia, or combinations thereof.
75 . A method of deterring terrestrial arthropods, the method comprises
a) providing a composition of claim 61 ; and b) treating a surface or an aqueous solution with the composition;
wherein the a mosquito, a tick, a fly, a cockroach, an arachnid, or an insect.Join the waitlist — get patent alerts
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